Hydrogen Peroxide → 4,5-Epoxy-6-methylenandrostane-3,17 dione

HRID 620677Notes

Reaction equation

HRID 620677 reaction equation
[CH2:1]=[C:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[OH:23]O.[OH-].[Na+].O>CO>[O:23]1[C:19]23[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]12)[C@@H:13]1[C@H:4]([C@H:5]2[C@@:9]([CH2:11][CH2:12]1)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]2)[CH2:3][C:2]3=[CH2:1]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 129518006-Methylideneandrost-4-ene-3,17-dione

Product 1

HCID 186310944,5-Epoxy-6-methylenandrostane-3,17 dioneYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-methylenandrost-4-ene-3,17-dione (5 g, 16.7 mmole) in methanol (200 ml) cooled at 0° C. is added a cold 36% hydrogen peroxide solution (17 ml) and a cold 2% sodium hydroxide aqueous solution. The resulting reaction mixture is stirred at 0°-5° C. during 24 hrs, then it is poured into iced water (1400 ml) with vigorous stirring. The resulting precipitate is filtered, washed with water and dried in vacuo. There are obtained 4.2 g (80% yield) of the title compound,

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dfe15067ecc24b0c8dff84af0d7ef37c
Source dataset
uspto-grants-1989_04
Patent number
US04822528

Reaction notes

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